3-(Chloromethyl)-5-(4-chlorophenyl)-1,2-oxazole → {6-[5-(4-Chloro-phenyl)-isoxazol-3-ylmethoxy]-benzofuran-3-yl}-acetic acid methyl ester

HRID 1296042Notes

Reaction equation

HRID 1296042 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[O:7][CH:6]=1.Cl[CH2:17][C:18]1[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[O:20][N:19]=1>C(#N)C>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][CH2:17][C:18]3[CH:22]=[C:21]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=4)[O:20][N:19]=3)=[CH:13][C:8]=2[O:7][CH:6]=1

Participants

4

Reactant 2

HCID 14811003-(Chloromethyl)-5-(4-chlorophenyl)-1,2-oxazoleHCID 20770861Methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetate

Product 1

HCID 20770854{6-[5-(4-Chloro-phenyl)-isoxazol-3-ylmethoxy]-benzofuran-3-yl}-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (6-hydroxy-benzofuran-3-yl)-acetic acid methyl ester (0.41 g, 2.0 mmol) and commercially available 3-(chloromethyl)-5-(4-chlorophenyl)isoxazole (0.46 g, 2.0 mmol) were combined in 15 ml of acetonitrile. The mixture was stirred at room temperature for 64 hours and filtered. The insoluble material was washed on the funnel several times with fresh acetonitrile. The bulk of the solvent was evaporated, and the residue was partitioned between 200 ml of ethyl acetate and 150 ml of brine. The layers were separated, and the aqueous layer was extracted with fresh ethyl acetate (2×100 ml). The combined organic layers were back-washed with brine (2×150 ml), then dried over anhydrous sodium sulfate and concentrated. The crude product was purified by normal phase chromatography. mp 136–137° C.; MS m/z 397 (M−1).

Workup

  1. filtrationfiltered
  2. washThe insoluble material was washed on the funnel several times with fresh acetonitrile
  3. customThe bulk of the solvent was evaporated
  4. customthe residue was partitioned between 200 ml of ethyl acetate and 150 ml of brine
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with fresh ethyl acetate (2×100 ml)
  7. washThe combined organic layers were back-washed with brine (2×150 ml)
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe crude product was purified by normal phase chromatography

Sources & evidence

ORD record
ord-6f3af1e2c487425984e98165ac0cd207
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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